Which pair of products would result from the acid cleavage of phenyl propyl ether with HBr at an elevated temperature?

Phenol and 1-propanol

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Bromobenzene and 1-propanol

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Bromobenzene and 1-bromopropane

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Phenol and 1-bromopropane

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Solution

The correct option is D Phenol and 1-bromopropane
Ethers can be reactive under drastic reaction conditions (high temperature, high concentration) due to the cleavage of the C-O bond in presence of HBr.
$Ether + HBr \to Alkyl bromide + Alcohol .$ Halide attacks at less hindered site to produce alkyl halide.
$C_{6} H_{5} - O - C_{3} H_{7} + H B r △ \to C_{6} H_{5} - O H + C_{3} H_{7} B r .$

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Ethyl phenyl ether on boiling with conc. HBr gives

O_{2}

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